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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone structure

CAS No.: 84-58-2

Chemical Name:: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Synonyms: 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE;4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile;Dichlorodicyanobenzoquinone;2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE;2,3-DICHLORO-5,6-DICYANOBENZOQUINONE;1,2-Dichloro-4,5-Dicyanobenzoquinone;Dichlorodicyanoquinone;2，3-Dicyano-5，6-dichlorobenzoquinone;2,3-dichloro-5,6-dicyano-4-benzoquinone;2,3,5,6-Dichlorodicyanoquinone

CBNumber:: CB5751792

Molecular Formula:: C8Cl2N2O2

Molecular Weight:: 227

MDL Number:: MFCD00001593

MOL File:: 84-58-2.mol

MSDS File:: SDS

Last updated:2023-11-16 09:24:38

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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Properties

Melting point	210-215 °C (dec.)(lit.)
Boiling point	301.8±42.0 °C(Predicted)
Density	1.7500 (estimate)
storage temp.	Store below +30°C.
solubility	Soluble in benzene, methanol, acetic acid and dioxane.Slightly soluble in chloroform,, dichloromethane.
form	Crystalline Powder or Crystals
color	Yellow to orange
Water Solubility	reacts
Sensitive	Moisture Sensitive
Merck	14,3063
BRN	747939
InChIKey	HZNVUJQVZSTENZ-UHFFFAOYSA-N
CAS DataBase Reference	84-58-2(CAS DataBase Reference)
EWG's Food Scores	1
FDA UNII	1H5KD39UH7
NIST Chemistry Reference	1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2)
EPA Substance Registry System	1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS06

Signal word

Danger

Hazard statements

H301

Precautionary statements

P264-P270-P301+P310-P405-P501

Hazard Codes

Risk Statements

25-29-41-37/38-20/21-23/24/25

Safety Statements

22-24/25-37-45-36/37-26-36/37/39

RIDADR

UN 3439 6.1/PG 3

WGK Germany

RTECS

GU4825000

TSCA

Yes

HazardClass

6.1

PackingGroup

HS Code

29269095

NFPA 704

	1
3		2
	W

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone price More Price(50)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	D60400	2,3-Dichloro-5,6-dicyano-p-benzoquinone 98%	84-58-2	5g	$30	2024-03-01	Buy
Sigma-Aldrich	D60400	2,3-Dichloro-5,6-dicyano-p-benzoquinone 98%	84-58-2	10g	$53.6	2024-03-01	Buy
TCI Chemical	D1070	2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T)	84-58-2	25g	$104	2024-03-01	Buy
TCI Chemical	D1070	2,3-Dichloro-5,6-dicyano-1,4-benzoquinone	84-58-2	5G	$30	2021-12-16	Buy
TCI Chemical	D1070	2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T)	84-58-2	250g	$632	2024-03-01	Buy

Product number	Packaging	Price	Buy
D60400	5g	$30	Buy
D60400	10g	$53.6	Buy
D1070	25g	$104	Buy
D1070	5G	$30	Buy
D1070	250g	$632	Buy

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Chemical Properties,Uses,Production

Description

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has a variety of applications. DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of quinolones and an oxidizing agent used to synthesize steroids. Additionally, DDQ is used with Ph3P to synthesize 1,2-benzisoxazoles.

Chemical Properties

yellow to orange powder

Uses

An oxidizing agent, especially in steroid synthesis.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is used as a reagent for oxidative couplings and cyclization reactions and dehydrogenation of alcohols, phenols and steroid ketones. It is also used in the synthesis of 1,2-benzisoxazoles. It is a useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.

Preparation

The first synthesis of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was described by J.Thiele and F.Guntber in 1906. However, no interest was shown in the compound until Linstead and co-workers discovered its extraordinary potency as a dehydrogenating agent. Its oxidation potential is greater than that of any other known quinone.
2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation

Application

2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) can be used as:
A deprotecting reagent for a variety of compounds, such as thioacetals, acetals, and ketals.
An electron-transfer reagent for the synthesis of quinolines from imines and alkynes or alkenes.
An effective reagent for the benzylic and allylic C?H functionalization.
An oxidizing agent for the synthesis of functionalized furans and benzofurans.
A reagent with Ph3P in an efficient synthesis of 1,2-benzisoxazoles.

Mechanism of action

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has many applications in the oxidation of various organic compounds such as ketones, alcohols, phenols, aromatic compounds, heterocyclic structures, etc. Apart from that, the presence of two chlorine atoms and two nitrile groups on the benzoquinone ring may also behave as a potential chlorinating agent. Consequently, DDQ could act simultaneously as the chlorinating agent and the oxidant. It can also remove the protective functional groups during deprotections of different chemical entities. For dehydrogenation by DDQ, the mechanism includes the transfer of hydride to the quinone oxygen followed by the transfer of a proton to the phenolate ion[1].

Safety

DDQ reacts with water to release highly toxic hydrogen cyanide (HCN). A low-temperature and weakly acidic environment increases the stability of DDQ.

Purification Methods

Crystallise DDQ from CHCl3, CHCl3/*benzene (4:1), or *benzene and store it at 0o. [Pataki & Harvey J Org Chem 52 2226 1987, Beilstein 10 H 902, 10 II 635, 10 IV 3521.]

References

[1] Alsharif, Meshari A. et al. “DDQ as a versatile and easily recyclable oxidant: a systematic review.” RSC Advances 47 (2021): 29826–29858.

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone synthesis

Synthesis of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone from 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-, compd. with 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (1:1)

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Preparation Products And Raw materials

Raw materials

Carbon tetrachloride 3,6-Dihydroxyphthalonitrile

Preparation Products

1-Benzofuran-5-carbaldehyde 2,6-Di-tert-butyl-p-benzoquinone 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran N-methylacridine 9-Methylene-9H-fluorene

2,7-Dibromophenanthrene 4-Methyl-3-nitrobenzonitrile

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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Suppliers

Global( 509)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Hangzhou Qiwei Pharmatech Co.,Ltd	13282840061	mw@qwpharmatech.com	China	109	58
Hebei Yanxi Chemical Co., Ltd.	+8617531190177	peter@yan-xi.com	China	5857	58
Firsky International Trade (Wuhan) Co., Ltd	+8615387054039	admin@firsky-cn.com	China	427	58
Capot Chemical Co.,Ltd.	+86-（0）57185586718 +86-13336195806	sales@capot.com	China	29791	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21634	55
Zjartschem	+86-571 87238903	jocelynpan@zjarts.com	CHINA	988	58
Tianjin Zhongxin Chemtech Co., Ltd.	+86-022-66880623 +8618622897568	sales@tjzxchem.com	China	563	58
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29884	58
NINGBO INNO PHARMCHEM CO., LTD.	13867897135	sales@nbinno.com	CHINA	923	58
Hubei Jusheng Technology Co.,Ltd.	18871490254	linda@hubeijusheng.com	CHINA	28172	58

Supplier	Advantage
Hangzhou Qiwei Pharmatech Co.,Ltd	58
Hebei Yanxi Chemical Co., Ltd.	58
Firsky International Trade (Wuhan) Co., Ltd	58
Capot Chemical Co.,Ltd.	60
Henan Tianfu Chemical Co.,Ltd.	55
Zjartschem	58
Tianjin Zhongxin Chemtech Co., Ltd.	58
career henan chemical co	58
NINGBO INNO PHARMCHEM CO., LTD.	58
Hubei Jusheng Technology Co.,Ltd.	58

Application of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)
DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of qu....
Feb 16，2022

View Lastest Price from 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-21	2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 84-58-2	US $0.00 / Kg/Drum	1KG	99%	200mt/year	Jinan Finer Chemical Co., Ltd
2024-10-25	DDQ 84-58-2	US $0.00 / kg	1kg	99	20tons	Hebei Yanxi Chemical Co., Ltd.
2024-10-25	DDQ 84-58-2	US $0.00 / kg	25kg	98%	10MT/Month	Hebei Yanxi Chemical Co., Ltd.

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
US $0.00 / Kg/Drum
99%
Jinan Finer Chemical Co., Ltd

DDQ
84-58-2
US $0.00 / kg
99
Hebei Yanxi Chemical Co., Ltd.

DDQ
84-58-2
US $0.00 / kg
98%
Hebei Yanxi Chemical Co., Ltd.

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Spectrum

DDQ(84-58-2)MS DDQ(84-58-2)¹³CNMR DDQ(84-58-2)IR1 DDQ(84-58-2)IR2 DDQ(84-58-2)Raman

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2,3-Dichloro-5,6-dicyano-para-benzoquinone 2-dicarbonitrile,4,5-dichloro-3,6-dioxo-4-cyclohexadiene-1 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE ( DDQ ) 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE ( DDQ ) 99 DICHLORO(2,3-)-5,6-DICYANO-4-BENZOQUINONE LABOTEST-BB LT00005588 1,2-DICARBONITRILE-4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE 2,3-DICHLORO-5,6-DICYANOQUINONE 4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,2-CARBONITRILE 4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,2-DICARBONITRILE 2,3-Dichloro-5,6-dicyano-1,4-Benzoquinone(DDQ) 4,5-dichloro-3,6-dihydroxy phthalonitrile 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINON 2,3-Dichloro-5,6-dicyanobenzoquinone, 98+% 2,3-Dichloro-5,6-dicyanobenzoq 1,2-Dichloro-4,5-dicyano-p-benzoquinone 2,3-Chloro-5,6-dicyanoquinone 2,3-Dichloro-5,6-dicyano-p-quinone 2,3-Dicyano-5,6-dichloro-2,5-cyclohexadiene-1,4-dione 3,6-Dihydro-3,6-dioxo-4,5-dichloro-1,2-benzenedicarbonitrile 4,5-Dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrile DDQ(0-6℃) 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone,98% 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE pure 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile, DDQ 3-Dichloro-5 4-benzoquinone (DDQ) 6-dicyano-1 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98% 100GR 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98% 10GR 4-Cyclohexadiene-1,2-dicarbonitrile,4,5-dichloro-3,6-dioxo-1 2,3-Dichloro-5,6-dicyano-p-benzoquinone,4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile, DDQ 2,3-Dichloro-5,6-dic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 1,2-Dichloro-4,5-dicyano-3,6-dioxocyclohexa-1,4-diene Two-5,6- two2,3-chlorinecyanogenp-benzoquinone 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% DDQ 2 3- two 6- two -5 chlorine cyanide, p-benzoquinone 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 2,3-Dichloro-5,6-dicyano-p-benzoquinone, 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile 2,3-DichL oro-5,6-dicyano-1,4-benzoquinone 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone > 2,3-Dichoro-5,6-dicyano-1,4-benzoquinone 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone ISO 9001：2015 REACH Dichloro-5,6-Dicyano-1,4-Benzoquinone(DDQ) 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) pure, 98% 2,3-DICHLORO-5,6-DICYANO-p-BENZOQUINONE For Synthesis 1,2-Dichloro-4,5-Dicyanobenzoquinone 2,3,5,6-Dichlorodicyanoquinone 2,3-dichloro-5,6-dicyano-4-benzoquinone 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE 2，3-Dicyano-5，6-dichlorobenzoquinone 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Dichlorodicyanobenzoquinone Dichlorodicyano-p-benzoquinone